Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton

Jane Totobenazara; Heloua Haroun; Julien Rémond; Karim Adil; Fabrice Dénès; Jacques Lebreton; Catherine Gaulon-Nourry; Pascal Gosselin

doi:10.1039/c1ob06776a

Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton

Jane Totobenazara, Heloua Haroun, Julien Rémond, Karim Adil, Fabrice Dénès, Jacques Lebreton, Catherine Gaulon-Nourry^*, Pascal Gosselin

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spiro epoxide 2a was treated with MABR, yielding stereoselectively the cyclohexane carbaldehyde 9.

Original language	English (US)
Pages (from-to)	502-505
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	3
DOIs	https://doi.org/10.1039/c1ob06776a
State	Published - Jan 21 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton",

abstract = "Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spiro epoxide 2a was treated with MABR, yielding stereoselectively the cyclohexane carbaldehyde 9.",

author = "Jane Totobenazara and Heloua Haroun and Julien R{\'e}mond and Karim Adil and Fabrice D{\'e}n{\`e}s and Jacques Lebreton and Catherine Gaulon-Nourry and Pascal Gosselin",

note = "Funding Information: I thank A. Kost, D. Williams, and J. Washizaki for excellent electron microscopy and photography. This work was supported by grants from the National Science Foundation and the National Institute of General Medical Sciences.",

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T1 - Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton

AU - Totobenazara, Jane

AU - Haroun, Heloua

AU - Rémond, Julien

AU - Adil, Karim

AU - Dénès, Fabrice

AU - Lebreton, Jacques

AU - Gaulon-Nourry, Catherine

AU - Gosselin, Pascal

N1 - Funding Information: I thank A. Kost, D. Williams, and J. Washizaki for excellent electron microscopy and photography. This work was supported by grants from the National Science Foundation and the National Institute of General Medical Sciences.

PY - 2012/1/21

Y1 - 2012/1/21

N2 - Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spiro epoxide 2a was treated with MABR, yielding stereoselectively the cyclohexane carbaldehyde 9.

AB - Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spiro epoxide 2a was treated with MABR, yielding stereoselectively the cyclohexane carbaldehyde 9.

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DO - 10.1039/c1ob06776a

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AN - SCOPUS:84055178587

SN - 1477-0520

VL - 10

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JO - Organic and Biomolecular Chemistry

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IS - 3

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Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton

Abstract

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